Hydrochloric Acid → Hydrochloric Acid

HRID 40642Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:18][C@H:17]2[NH:19][CH2:20][C@@H:12]1[CH2:13][CH:14]=[CH:15][CH2:16]2.[S:21]1[CH:25]=[C:24]([C:26](=[O:30])[CH2:27][CH2:28][Cl:29])[C:23]2[CH:31]=[CH:32][CH:33]=[CH:34][C:22]1=2.CCN(C(C)C)C(C)C.Cl>C(OCC)C.CN1C(=O)CCC1>[S:21]1[CH:25]=[C:24]([C:26](=[O:30])[CH2:27][CH2:28][N:19]2[CH2:20][CH:12]3[N:11]([C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)[CH2:18][CH:17]2[CH2:16][CH:15]=[CH:14][CH2:13]3)[C:23]2[CH:31]=[CH:32][CH:33]=[CH:34][C:22]1=2.[ClH:29]

Participants

Conditions

Temperature: 160 °C

Procedure

Z-(1S,6S)-7-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-ene (50 mg, 0.189 mmol), 1-benzo[b]thiophen-3-yl-3-chloro-propan-1-one (50 mg, 0.22 mmol) and DiPEA (0.1 mL, 0.57 mmol) were placed in a μW tube with NMP (2 ml), and heated to 160° C. for 900 sec. The solvent was evaporated to yield a crude oil, which was purified via reverse phase chromatography (20% CH3CN to 90% CH3CN in water) to yield a residue which was then treated with 1N HCl in diethyl ether. The solvent was then evaporated under reduced pressure to yield the title compound as its corresponding HCl salt, as a residue.

Workup

customThe solvent was evaporated
customto yield a crude oil, which
customwas purified via reverse phase chromatography (20% CH3CN to 90% CH3CN in water)
customto yield a residue which
customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record: ord-a1f0d3f3e75042718c6d800ec61a4950
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530475B2

Reaction notes

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